Head to Head includes singles and doubles results.
| 05/20/23 | Jackson Phillips over Bob Leopardi | 6-2; 6-3 | |
| 03/12/23 | Jackson Phillips over Bob Leopardi | 6-4; 6-4 | |
| 02/23/23 | Jackson Phillips over Bob Leopardi | 7-5; 6-1 | |
| 09/10/22 | Jackson Phillips over Bob Leopardi | 4-6; 6-2; 6-1 | |
| 07/19/22 | Jackson Phillips over Bob Leopardi | 6-4; 4-6; 6-4 |
